


Mature Tastes

by DraceDomino



Category: My Little Pony: Equestria Girls
Genre: Breeding, Cock Worship, F/M, Impregnation, Loss of Virginity, MILFs, Older Woman/Younger Man, Oral Sex, Shota, Threesome - F/F/M, Vaginal Sex
Language: English
Status: Completed
Published: 2017-12-20
Updated: 2018-08-04
Packaged: 2019-02-17 07:03:58
Rating: Explicit
Warnings: Underage
Chapters: 4
Words: 19,288
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13071642
Author URL: https://archiveofourown.org/users/DraceDomino/pseuds/DraceDomino
Summary: There's a new student at Canterlot High, and none of the teachers can seem to keep their hands off him! He may be young, but that won't stop Aero from charming and breeding Celestia, Luna, and plenty of others!Shota story, starring the commissioner's OC!





	1. Chapter 1

Mature Tastes  
Chapter One: First Time for Everything  
-by Drace Domino

Principal Celestia wasn’t entirely sure how things had gotten this far, but there was no going back now. The second her hand had lowered to rest in the center of her newest student’s lap, the second she felt his shaft throbbing against her palm through the fabric of his jeans, she had already crossed a line that teachers weren’t meant to cross. It was clear that she knew as much by the look on her face, and it took her a few seconds to really process just what she had done. While she thought her fingers found themselves rolling gently back and forth and squeezing at the sculpted weight underneath them, tracing along the outline of an impressive cock for a boy of his age.

Her new student; Aero Ruinwing. Principal Celestia had only met the boy a few minutes ago when he showed up in her office, there to report for his very first day of class at Canterlot High. A transfer from a different school, it was pretty clear he was going to receive a very different sort of education than that which he was used to at this new place. For his part, the handsome young man remained perfectly still within his seat, though he did give a nervous swallow while he looked up at the older woman past the line of silver bangs hanging just before his eyes.

“Ah...uhm...Principal Celestia?” He had to pause to take a breath, for his young body was already pulsing with excitement. How could it not? This gloriously beautiful older woman was crouching down right by his chair, her pearl-pink fingers still squeezing his member through his jeans. It was the first time anyone, let alone a teacher, had fondled him in such a way and part of the boy was afraid to ruin the moment. “Do...do you know what you’re touching…?”

He was kind enough to give Principal Celestia that one out; that one escape from how their first meeting had gone. If she pulled her hand back and returned to her desk they could simply go about the orientation as if nothing had happened, as if she hadn’t crossed some horrible boundary in a direct violation of her teaching ethics. For a split second the thought of taking Aero up on his offer seemed to cross the older woman’s mind, but sure enough her hand continued to linger in place right atop his shaft. In fact, as she looked up to meet Aero’s gaze once more, her fingers even tightened to give him another slow, long squeeze.

“I do indeed.” She finally spoke up in response, and a tiny smile pulled at the corner of her lips. She used her free hand to move out and hold the edge of Aero’s seat, balancing herself as she continued to crouch before him. Dressed in her typical blazer and plants that made her instantly recognizable as Canterlot High’s top teacher, she would’ve looked downright professional save for the alluring, seductive smile playing on her face. She took a long breath before speaking again, and when she did her hand pulled slowly up and down across Aero’s lap, making sure she was paying every inch of his young manhood attention with fondling fingers. “Aero, perhaps we should take a moment to reflect on what our first meeting has been like. I’ll admit, when I first came to work today I wasn’t in the greatest of moods. Our school has been subject to a bit of chaos over the past few months, and the recent Friendship Games was easily the most stressful time I’ve had in a while. So when I found out we were getting yet another student my immediate thought was ‘Great, another young person I can fail to protect from all this magical nonsense.’”

“Magical nonsense…?”

“It’s...not important.” Celestia quickly shook her head, and offered Aero a smile. Her eyes darted from the boy’s handsome features to the two braids hanging down from either side of the back of his head; long trails of tightly wrapped hair that flared behind him in stylish fashion. After just a few seconds of appreciative admiring she let her gaze flicker back to his face, where she met his eyes as she continued. “So I stepped into my office today in a bad mood. I’m stressed about the school, I just had an argument with my sister, and if I’m being completely honest...it’s been far, far too long since I’ve handled one of these.” Once more her fingers tightened, giving Aero such a squeeze that the young man gasped and lifted up slightly from his chair. “So after talking to you for a few minutes and noticing this bulge of yours, I…”

“I’m sorry…” Aero murmured, a blush lining his charming features almost instantly. He fidgeted in place underneath Celestia’s grasp, almost feeling as if this whole thing was suddenly his fault. “Sometimes I can’t control it, especially when I’m talking to someone as pretty as you are. Believe me, I wish I could keep it down, but...uh…”

“But it’s quite a lot to keep in check.” Celestia chuckled a bit, and scooted just a little closer in her crouching position. Soon her hand had pressed flat against his jeans before creeping up inch by inch, moving closer and closer to the zipper. She let her fingers dangle there for a split second; teasing at the metal clasp but not quite ready to pull it down. “I could help you with that, Aero. If you’d like your principal’s assistance, of course.”

“Are you are?” Aero asked, blushing again as his chest started to rise and fall in a faster pace. “I mean, I...I think I’d love that, but...should you?” Principal Celestia, after only a few short seconds, merely smiled and let her other hand drift out. She pressed her fingers and her bare, smooth palm to Aero’s cheek and allowed her touch to sweetly caress him; soon cupping his cheek and bringing his head forward a few inches. While she did so her own head drifted near, and her opposite hand pinched the edge of his zipper to start slowly pulling it down. By the time the zipper was all the way to the bottom Celestia had pressed a warm and tender kiss to the corner of Aero’s lips; hardly enough for a full kiss of intimate contact, but enough to ease his concerns. As she pulled back and allowed both hands to drop toward his lap, the older woman gave him a playful wink.

“Let’s just keep it between us, hmm?” She asked, just as those smooth, soft fingers slithered into his jeans to recover his length. Aero gave a sudden gasp as he felt her grasp him without his pants in the way, for those pearl-pink digits fished right into his boxers to find the prize they sought. Before long she had freed him from his restraints and his shaft stuck straight up from the center of his lap, a beautiful length that wasn’t just a rival to any Celestia had ever seen, but a superior. The older woman’s eyes went wide as she first saw it, her throat tightening and her cheeks tinting with a noticeable blush. As she closed both hands around his shaft Aero gave a sudden twitch, his hands dropping down the wooden chair and grasping firmly upon the edges. This was all new territory to him, and it felt like if he didn’t hold on tight he’d go spinning right out of his chair. When Celestia offered him another whisper, it managed to excite him even further and intensify that spinning, light headed sensation. “Aero, dear, your cock is amazing.”

“Uh, thanks, Principal Celestia…” Aero murmured, and bit down on his bottom lip as he watched the older woman’s head draw closer to his lap. She made sure to keep constant eye contact with Aero as her lips parted and her tongue rolled forward, and by doing so ensured that he could gaze into the eyes of the first woman that wrapped her mouth around his cock. Her lips closed about the tip and her tongue pressed flat to the head, slowly working back and forth to make the young man shudder in his seat. Still rather overwhelmed by it all Aero could merely tightening his grip on the edges of the chair, his eyes drifting close despite how very dearly he wished he could keep watching. Everything just felt too good! The warmth of Principal Celestia’s mouth, the wetness of her wiggling tongue, and the smooth grip of her hands as she slowly, steadily pumped his shaft. It was a different sensation from anything he had ever experienced for himself, and it became astonishingly clear in a short amount of time just what the big deal was about sex. As Principal Celestia continued to slowly slurp up his inches, it took every ounce of strength in Aero’s body to lift his eyes open once more and not give in to simply melting in his seat. “That feels...it feels...I can’t even describe it!” In response, Principal Celestia merely gave a tiny chuckle with her lips smiling around his shaft, and she gave his member one more squeeze before picking up the pace.

Aero was learning a lot during his first day at Canterlot High, that much was certain. Heck, he was learning a lot during his first hour there. His legs slowly spread as much as they were able to give the older woman room to keep servicing him, and he was rewarded by Principal Celestia taking him down to new depths with every passing second. She pushed her head down along his throbbing length and pulled back up only to descend once more, and each time those smiling lips passed downward they managed to get a little bit deeper. Before too long she was bumping her nose against the fabric of his jeans, and he could tell that his girth was past her mouth and well into her throat by then. It didn’t seem to bother her; however, in fact it only seemed to encourage her further. The cock hungry older woman delighted in deepthroating her new student, still crouching there in a lewd state with her gorgeous glistening hair framing the sides of her face. Hair that looked so beautiful, so soft, that Aero couldn’t resist the urge to reach out and grasp it any longer.

He was nervous as he took Celestia’s hair in both his hands, but the older woman looked up at him with a playful smile when she felt his fingers sink into her flowing locks. She was deepthroating him at the time and when he made that bold gesture she pulled her mouth up once more; just enough that her lips left the tip so she could speak to him. In those brief seconds Aero could see his cockhead glistening wet from his principal’s spit, while threads of it connected to her lips and danced with every word she spoke.

“Don’t be afraid to touch me, Aero.” Principal Celestia cooed, and swung his member back and forth so it slapped her playfully on her parted lips. She even wiggled her tongue out from her mouth and let it dance back and forth underneath his tip, sending even more shockwaves of pleasure through him. “Are you enjoying what I’m doing for you?”

“It’s the best thing I ever felt.” Aero admitted without hesitation, and once more found himself nibbling on his bottom lip. What could he say? How could he respond to this unexpected turn of events? He had expected his first day at Canterlot High to be boring beyond all measure, but this? He couldn’t help but wonder one thing, and his voice quivered out in a curious tone to the older woman. “Do...do you do this for all your students?” Celestia merely gave a delightful laugh, and pressed a long smooch to the side of his shaft before responding.

“Just you.” She purred, and made a point of letting Aero watch her lick his cock from the base all the way up to the tip, complete with a long coil of spit bouncing from the bottom edge of her tongue. She didn’t mind looking a bit messy - not when it meant making her new friend throb all the harder. “There’s something about you. And there’s definitely something about this beautiful thing right here.” She gave another squeeze of his length, and winked.

That was good enough for Aero! With a smile he was finally bold enough to pull at Principal Celestia’s hair; his fingers tightening within her locks and ushering her mouth to his tip once more. Celestia was just about to wrap her lips around that lovely length once more before a sudden noise filled the room - so piercing and so loud it made both of them suddenly jump. A loud knock came to Principal Celestia’s door, and as she looked up with a panicked expression on her face she quickly started to lift herself up to her heels.

“Sister, it’s me.” There was a female voice coming from the other side of the door, one that Aero hadn’t yet had the pleasure of meeting. He just watched as Principal Celestia did her best to wipe the spit away from her face, and even snatched up a mirror to take a quick look at herself. “Can we talk about earlier?”

“Uh...just...just a minute, Luna!” Principal Celestia stammered, and gazed down at her student with his big, wet cock sticking straight up from his lap. It was desperately difficult not to throw herself onto it all over again, but she had to keep herself content by reaching down to tease the tip with a finger, and whisper in a hurried voice. “Just...stay right here, and don’t say anything!”

Not only would Aero not say anything, he wasn’t entirely sure he’d move ever again. The knock on the door and the sound of a third party’s voice was enough to scare the sense out of the young man, and he sat there with his cock still rock hard as Principal Celestia ushered herself to the door. She had the foresight to block the entrance with her body as she opened it just a crack, making sure that her sister didn’t have any chance to step inside the room or even see what was hiding behind her.

“What is it, Luna?” Celestia sounded hurried and rushed - understandable considering what she had waiting for her in the office. “I’m...I’m really busy right now.”

“I’m sorry, Celestia, I just wanted to apologize for earlier.” The smooth tone was that of Vice Principal Luna, though no matter how Aero twisted in his seat he couldn’t manage to get a look at her. At least not without risking being seen, himself, and he was in no condition for that! “We haven’t had a fight like that in a while. I know you’re under a lot of stress these days, and I’m...I’m just sorry.”

“Yeah, me too.” Principal Celestia chimed in, and impatiently drummed her fingers on the top rim of the door. “I’m sorry too, Luna. Thanks for dropping by, I really need to get to wo-”

“Celestia, are you okay?” Vice Principal Luna’s voice chimed up again, sounding curious and concerned. She even let a hand drift up to feel her sister’s cheek, noting that it was slightly damp. “Your color’s all drained and it feels like you’re running a fever. Should I call for the nurse?”

“No! No, I’m fine, Luna.” Celestia quickly explained, still doing her best to block her sister from entering. When she thought of a quick excuse her voice dropped low, and she whispered in a tiny, embarrassed tone. “I...I was upset after our argument, and I was crying a little. But I’m fine now.”

“Oh...oh I’m so sorry!” For a moment it seemed like nothing Celestia said would manage to make the conversation end quicker, and it was rough for all parties involved. The guilt that ebbed in Luna, the awkwardness for Celestia in trying to keep her activities a secret, or the fact that poor Aero was left sitting there with his cock throbbing, practically aching for more attention. Thankfully Celestia managed to break away from the conversation by leaning forward and giving her sister a quick kiss on the cheek; a kiss that left her lips marked with a tiny wet mark hinting of Aero’s flavor.

“It’s okay, Luna, really! I love you, sister, I just need some time!” After that kiss she pushed her hand to her sister’s shoulder, and wedged her out of the way so she could close the door. “I actually think I’m going to take a small nap during lunch, so...I’ll see you after!”

“Oh, okay, would you like me to pick you up anythi-”

The door slammed on Luna and Celestia quickly moved to lock it, breathing a sigh of relief as she turned her attention back towards the young man. Even though they had nearly been caught it clearly didn’t sway Celestia away from her planned course of action, and she set her gaze hungrily on the young man and his throbbing, spit-covered cock once more. With a smile she stepped forward and loomed tall over Aero, casting a shadow on the boy’s body to the point where it made him fidget in a nervous moment.

“Uh...is...is something wrong?” He asked, and deeply hesitated before asking the next question. “Should we stop…?” Oh, how he didn’t want to ask it, but it was the responsible thing. Thankfully, it wasn’t a question that Celestia was prepared to humor with a response.

“...I need to get you inside of me. Now.” Was her simple reply, just as her hands drifted down to the edge of her belt. As she snapped the strap through the buckle her eyes flickered from Aero’s cock to his face, and her grin grew by leaps and bounds the longer she pondered her decision. “Aero? Time to lose your virginity.”

Aero, being the good student that he was and so very willing to please his principal, offered a sharp nod and a quick voice.

“Yes, ma’am!”

\---

Aero was left marvelling at his first real look at a woman’s pussy not long after, for it didn’t take long for Celestia to drop her slacks and panties to the floor and step forward. For the moment she still wore that brown blazer set overtop a CHS sports jersey, and she was so eager to get her new young friend inside of her that she didn’t seem particularly concerned about stripping further. As she stood in front of Aero she let her legs spread while a single hand moved down to her shaved slit, pulling the folds apart and letting him see the glistening pink that was waiting for his cock.

“I can’t wait to feel you deep inside of me, Aero.” She whispered and teased him by slipping her middle two fingers into her pussy, probing slow and gently mere inches before his eyes. “We just have to be careful...can’t let you cum inside of me. You wouldn’t want to knock up an old woman like me during your first time, right?” The laugh that flowed from her was sweet and charming, and as she stepped up closer she allowed her fingers to gently pop from her folds. She moved to stand straddling Aero’s lap, but before she lowered herself down to envelop his cock in her warm, wet folds she stretched the same hand forward to offer her center two fingers to Aero’s mouth. She let those glistening fingers draw closer and closer to his lips, speaking up just as he was able to catch the scent of her pussy. “...care for a taste?”

As if she had to ask. Aero just smiled and let his lips pull up and over Celestia’s fingers, his tongue moving to sweep in between them and collect the nectar they glistened with. The thrill of a woman’s excitement was firmly on his tongue by now, and it encouraged Aero to take Celestia’s hips in his hands. He was pulling her down now, just as eager as the mature woman was to join with her, and he continued to suckle at her fingers as she lowered herself in a smooth, swift motion. The first touch of her nethers against the tip of his cock came as a shock to them both, and Celestia pulled her hand from his lips so she could reach both of them around the back of his neck. For a moment her gaze was gentle and tender; as if the sex-mad older woman that had been teasing him to that point was briefly replaced with a kind, considerate educator.

“Here we go...I hear a boy never forgets his first.” Celestia cooed, and her hands found a spot at the base of Aero’s braids, gripping gently as she started to spear herself against his shaft. Both Aero and Celestia fell silent as the first few inches penetrated her; Celestia still shuddering from the taboo bliss of fucking her student, and Aero left staggered by his first experience with a real pussy. As the inches glided inside of her it felt like there was never any end to it - Celestia pushed herself down so slowly and gradually that it drew out the pleasure for what felt like long, glorious minutes. By the time she was perfectly seated on his cock and pressing her full breasts against his chest, both of them wore a line of sweat against their brow and a heavy blush across their face. Then, with Aero fully shoved inside of her, Celestia moved in close to kiss the boy on the corner of his lips before offering him another whisper. “Next time you’ll be doing a lot of the work, but for this first time? Let your principal take good care of you.”

And with that, she started to rock her hips. Aero’s voice broke out in a sudden and joyful cry as the older woman started to fuck him; not just due to the pleasure of the moment but for Celestia’s promise that this wouldn’t be their last time together. He was honestly eager to do as much as he could to help things along, but if his teacher felt like it was better than he sit back and learn for his first time, who was he to judge? His cock was wrapped tight in a wonderful warm slit that continued to slowly rock up and down across him, each time with Celestia bringing her bare lower half down to sit atop his jeans. Aero, still almost fully dressed, couldn’t help but to let his hands slip down to the sides of Celestia’s pearl-pink rump and give those full cheeks a tender squeeze.

“Hehe...enjoy my ass, hmm?” Celestia cooed, her hands tightening on Aero’s braids as she picked the pace up a little. By now the chair underneath them was starting to gently creak with every motion, rocking from Celestia’s momentum. As she loomed over Aero, fully exploiting their noticeable size difference, her mouth drew whisper-close to his own as she gave him another sweet and delicate tease. “...keep being a good boy, and you’ll get to know what that’s like, too.”

Poor Aero didn’t get a chance to respond to that, for no sooner than Celestia spoke did she mush her mouth forward to steal a kiss from her student. Their lips pressed firmly together as the older woman’s tongue snaked forward, chasing down Aero’s own and grappling it to the roof of his mouth. Aero was left moaning and tightening his hands against Celestia’s rump as he was given his first illicit kiss - today was a day for lots of firsts, it seemed! The kiss continued alongside Celestia’s steady thrusts, and the creaking of the chair was joined by the noise of Aero’s thick length pushing slow and deep into her wet, hungry hole.

From there it only continued, ensuring that while Aero was a boy when the morning started he was a man by the time lunch came. Celestia’s pussy gripped tight along his length and refused to let it go every time she pulled her hips up, ensuring that when she landed back in his lap that he went all the deeper. Her knees continued to slowly bend to keep the pace up, but before long Aero’s hands at her ass had figured out the rhythm to throw his own strength into it. She would’ve told him how proud she was, but her mouth was simply far too busy probing Aero’s own with her tongue.

Celestia was a woman well in need of a good fuck, and Aero was kind enough to provide it by sacrificing his virginity to the beautiful principal. In return for his kindness he enjoyed the unbridled pleasure of having his length milked by the older woman’s warm slit, giving him a pleasure that he had never known before that morning. The scent of Celestia’s hair, the feeling of her breasts pressed against his chest, the taste of her tongue...it was all simply glorious, and it was a miracle that Aero managed to hold on as long as he did. Proving that Celestia hadn’t made the wrong call in which student to throw herself at, he remained steadfast and hard inside the older woman’s pussy while she rode him for five, ten, fifteen minutes solid. Her motions were slow but steady, her kiss was a constant on Aero’s lips, and her hands took the time to explore every inch of him she could reach. Those long braids, his handsome cheeks, even under his shirt where her clever fingers explored a surprisingly fit and mature figure. It all spurned her on more and more, until finally Aero could sense that there was something happening with her.

“P...Principal Celestia...it feels...you’re…” Aero wasn’t even sure what he was trying to say anymore - wanting to speak up about a dozen topics all at once. His head was swimming as he thrust up into the older woman again and again, shuddering in shockwaves as pleasure ached across his figure. How could something so wonderful steel his strength so magically? Was it possible for something to feel so good that it left him helpless? If so, that was certainly what was happening in that moment. “Ohh, Principal, I’m...you better...stand up…!”

Celestia knew full well just what was about to happen, she knew that Aero was mere seconds away from flooding her pussy with rich, fertile cum. The responsible thing would be to stand up and prevent him from cumming inside of her, but she hadn’t gotten to such levels of profound pleasure by being responsible! Besides, even if she wanted to stand up and rob herself of the feeling of a womb filled of warm young cum, she couldn’t possibly hope to on those quivering knees. Celestia gripped Aero tighter, pulled at his braids, and gave a muted cry against his throat as her own orgasm rocked through her. She twitched, she spasmed, and her vibrations were just enough to push Aero over the same blissful edge.

The boy gasped as he felt his cock suddenly throb, unloading his cream deep into the older woman. To fuck a girl raw and flood her with cum during his first time was truly an accomplishment, but neither Aero nor Celestia had any idea just what an accomplish it was that early afternoon. All Aero knew was the warmth and wetness and overall joy that rushed through him, and all Celestia knew was the creamy delight that made her feel full and satisfied in a way she had never known. Neither one of them could tell - though they might have well guessed in more sensible times - that Aero’s seed was rushing deep into Celestia’s cervix, making a beeline for her tubes in the desperate hope of finding an egg to fertilize. Even as it happened within Celestia she knew nothing more than her blissful post-orgasmic joy, and the feel of Aero’s hair through her fingers. She leaned in close and pulled the boy into another warm, wet kiss as some of his cum oozed out of her pussy and down along his shaft, eventually pooling at his lap within his jeans. Things were a sticky mess down below, but the wet spots on Aero’s jeans were hardly the most permanent result of their first time together. Even as they kissed and fondled each other further, sperm were nestling to one of Celestia’s fertile eggs, attaching in the hopes of being chosen. The first time the Principal of Canterlot High ever fucked a student was also the first time she got pregnant - something she would look back on one day with a content smile and a full, round belly.

But for now, she and Aero were both unaware as their kiss parted and Celestia started to pull herself up to her feet. Cum still oozed from her slit as she moved to her nearby slacks, stepping over them and started to pull them up along her legs. As she got dressed Aero followed suit, tucking his softening cock back inside of his jeans and blushing tremendously. The scent in the room was overwhelmingly one of their lust, and long before Celestia spoke she moved to a nearby window to open it up in the hopes of getting some of their lusty stench from the room. After all, she had a parent teacher meeting in a half hour!

“Well, Mr. Ruinwing, it was certainly nice to meet you.” Principal Celestia finally spoke, and scooped a small yellow schedule from the corner of her desk before handing it to Aero. “As we were saying before I got...distracted, here’s your schedule for the current semester. I trust I won’t have any troublemaking from you, will I?”

“Oh, definitely not, Principal Celestia!” Aero smiled, taking the schedule and standing up to his full height. Still a solid foot or so shorter than the older woman, putting him right at the line of her breasts. “I promise, I’ll be a model student!”

“I’m sure of that.” The principal grinned, and moved a hand up to teasingly fix some of Aero’s hair that had gotten dishevelled during their session. The motherly hand of an older woman - fixing his hair, straightening his collar, and soon to be fondling his cock once more. “I’m expecting big things from you, Mr. Ruinwing.”

She would not be disappointed.

End of Chapter One.


	2. Sisters Sharing

**Summary for the Chapter:**

> Vice Principal Luna has been lonely lately, and it doesn't help that her big sister keeps bragging about the great sex she's having with her new boyfriend! When Luna comes home early one day, she sees something she shouldn't of...and joins in on something she never would've expected!

Mature Tastes  
Chapter 2: Sisters Sharing  
-by Drace Domino

It had been a long, frustrating week for Vice Principal Luna. Most weeks were; she was underappreciated by the students, did far more work than her older sister gave her credit for, and on top of all that it had been far, far too long since she had enjoyed the company of a man. Her argument with Principal Celestia last week was just another sign that poor Luna’s resolve was starting to slip, that she couldn’t keep being the demure little sister that always took everything on the chin and never put up much complaint. It was a stressful time for her under the very best of circumstances, but if there was one thing that absolutely did not help her attitude...it was her sister’s constant bragging.

It had only just started a week ago, and already Luna was sick of it. Celestia had found herself a new boyfriend, and had been completely unable to shut up about him. During the drive home she would talk about how sweet and handsome he was, and late at night she would brag about how massive his cock was and how well it filled her up. It had been a rough thing for Luna to have to listen to when she herself had been in a bit of a dry spell, but she had continued to do the good, sisterly thing and revel in her sister’s fortune while silently feeling jealous.

“I tell you, Luna, it just...mmm!” Celestia giggled on the car ride to school, pressing her thighs together as she was clearly unable to hold back her arousal at just the thought of her new, mysterious boyfriend. “He’s going to fuck me again tonight after class, so I’ll need you to come home a little later. Wouldn’t want to bother you with all the noise I’m going to make!”

“...fine, Sister.” Luna just rolled her eyes as her hands tightened around the steering wheel, keeping her vision focused on the road ahead. The fact that Celestia was so worked up at the idea of her boyfriend being inside of her again was enough to prove that he was a quality lay; nobody got that excited without good reason. “I guess I’ll just go to a fast food place and sit in the parking lot. Again.”

“It’s so sweet of you, Luna.” Celestia giggled, and moved a hand out to pet at the side of her sister’s hair, stroking down the dark locks with a gentle caress. “I promise, I’ll make it up to you! When you get a boyfriend I’ll do the same for you!”

Luna deeply, deeply doubted that her older sister would ever be so selfless...but considering the fact she doubted with the same passion her own ability to land a virile lover it didn’t really matter. She simply sighed with a heavy slump to her shoulders, and continued driving them to class.

“Sure you will, Celestia...sure you will.”

\---

After another long day of work and another equally long drive home while her sister twittered in delight over her impending fuck, Luna dropped Celestia off at home and did exactly as she had said. Another evening spent sitting in her car eating a salad and slowly sipping at a cup of tea, stewing in frustration over how the past few weeks had been going. The younger of the two sisters had always been the one to garner less attention; Celestia was brighter and more lively, more charismatic and able to claim the adoration of others. Sitting in her shadow had been something Luna had grown accustomed to, but as the seconds ticked by on her watch the vice principal’s patience started to wear thin. She had done some paperwork, finished her dinner, and even taken the time to E-mail their cousins Daybreaker and Nightmare Moon from her phone...and yet there was still at least a full hour to go before she could safely return home. As she stared at her watch stewing in her irritation, finally the younger sister gave a grunt and turned the car’s ignition once more.

“...to hell with it.” She murmured, and made a beeline for home. If she managed to sneak in the house and up to her bedroom, surely that wouldn’t be enough to bother her sister’s precious fling! By now she was positive that Celestia and her new boyfriend had most likely moved up to her bedroom, and that meant Luna would have a clear shot through the house to get to her own room in discrete privacy. As the vice principal murmured as she pulled into the driveway: “If I’m going to sit around all night being lonely, I’m going to do it in my own damned room.”

And with that, Luna slipped out of the car and started to head to the front door of the home she shared with her older sister. She moved quietly and carefully - even with her currently sour attitude, she was still considerate enough that she didn’t want to disrupt Celestia’s fun. By the time she slipped in the front door and very delicately closed it behind her; however, she already had the vague idea that she had made a mistake.

“Mmm, yes! Fuck me, fuck me, baby! Ohh, I just love being your little slut!” It was her sister’s voice filling the house; echoing from the walls and carrying a weighty, thick lust. Luna cringed at the sound of her older sister saying such filthy things, though she had to admit...she had never heard Celestia happier. “Your cock is so big, so thick…! I could let you fuck me all day and I’d never get used to it! Yes, yes, yes…!”

Luna’s cheeks darkened as she heard the steady sound of her sister’s pleasure, though she stuck to her plan of creeping through the house as quietly as possible. All she had to do was move from the living room to the kitchen, then up the stairs and hang a left into her bedroom. Surely, Celestia’s voice sounded so clear because she must have left the bedroom door open, and certainly it wasn’t because--

“Luna!”

\--or rather, it was entirely because Celestia was fucking her new boyfriend on the kitchen table. Luna stood in the doorway utterly frozen in place, her eyes wide and all the color immediately drained from her cheeks. Her purse dropped to the floor and her arms hung limp at her sides at what she had stumbled across, and immediately she knew...this wasn’t something she should be seeing.

Her beautiful sister was riding her boyfriend cowgirl-style on the kitchen table, and she was dressed for the occasion. Dark thigh-high nylons and a pair of fishnet gloves that rolled up nearly to Celestia’s shoulders, and a pair of leather boots that Luna was positive her sister had borrowed from her. Without asking, of course. Celestia’s body was otherwise completely bare; her full breasts exposed, her shoulders glistening with a thin line of sweat, and her shaved pussy wrapped around...wrapped around…

“...Celestia…” Luna’s voice was weak, as if she secretly hoped that it wasn’t true. “You’re sleeping with one of our students?!”

The new boy of CHS was laying on the kitchen table; by now with his head tilted to look at the vice principal from an awkward angle. He was stripped down bare and his silver hair was a dishevelled mess around his face, though his sheepish smile and enormous blush could easily be seen. He even lifted a hand up off of Celestia’s waist to give her a little wave, and his voice slipped into the room in an almost timid fashion.

“Uh...h-hi, Vice Principal Luna.” Aero Ruinwing greeted Luna to her own home, though he admittedly had a hard time thinking of just what to say afterwards. What could he possibly say after being caught fucking her adult sister on the same table they ate breakfast on? “How...How was school today for you?”

It was an awkward scene for all involved; from Luna not only catching her sister having sex but doing it with a much younger man, to Aero suddenly finding himself naked in front of yet another older woman, to Celestia unsure of whether she should pull herself up and try to cover herself, or simply just keep riding on Aero’s cock. After all, she was very close to her climax...and Aero was still rock hard. For a tense moment the three sat in each other’s presence in complete and total silence, and poor Vice Principal Luna’s head was spinning as she tried to think of what to say.

What could she say? Tell Celestia that what she was doing was forbidden and taboo? No doubt her older sister knew that and simply didn’t care! Could she tell Aero Ruinwing that he was being a bad boy and had to go home? Considering the circumstances, “bad boy” almost sounded like she was praising him! Could she just turn around, get back in the car, and go sit in a parking lot far, far away? No, because there was no going back after what she had witnessed. With her hands trembling and a line of sweat beginning to form at her brow, Luna finally started to speak with a quivering, yet still scolding voice.

“C...Cel...Celestia…” She began to stammer to her sister, before giving Aero a quick glance. Clearly, he was at least partly at fault in all of this! “...Aero. I’ll thank you both not to do...what you’re doing...on the same table I do puzzles on!”

That hardly seemed like the biggest issue between the three of them right now, but it was the only one that Luna could wrap her head around. She liked doing puzzles! She sure had plenty of time to do them in her sexless, lonely life, and now she wouldn’t be able to put them together without thinking about her older sister riding on a student’s ...throbbing ...thick ...cock. Luna’s throat tightened as she looked at the seam of where her sister’s pussy wrapped around the base of Aero’s shaft, and her eyes went even wider as Celestia started to pull herself up. It was a slow process but Luna could see Aero twitching, hear him gasping as Celestia’s slit pulled off of him with a slow pop, and his impressive length flopped forward glistening and wet. Aero’s first instinct was to try and cover himself, though even if his hands could’ve reasonably blocked the sight of his massive member - which they couldn’t - there was a presence at work that wouldn’t let him. As he tried, Celestia simply squeezed in with her thighs, keeping Aero from moving much underneath her.

“Don’t be shy, Aero. You have no reason for it.” Celestia finally purred, and with a hand moved forward to gingerly, delicately wrap her fingers around that glistening shaft. She was disappointed to have it pulled from her pussy, but delighted to feel it throb within her grasp. With a playful smile Celestia’s eyes set across the room to her blushing sister, and the words that followed from her lips were enough to make the room’s other two inhabitants quake with surprise. Delivered in a tone that was sultry, sweet, and fully aware of the sinful implications, Celestia’s voice flowed forward. “Luna? Do you want to go for a ride…?”

Young Aero was tense as he laid there on the table, still pinned under his principal’s weight. His cock was wrapped in a veil of pleasure he couldn’t possibly deny, still wet from Celestia’s pussy and now gently squeezed by her careful fingers. Over the past week he had fucked the older woman what felt like hundreds of times, and though he never failed to satisfy her it was always clear between them that Celestia was the more experienced, more practiced hand. If he had learned nothing else during their brief time together, it was that if he trusted the older woman his cock would be well rewarded. As such, he didn’t bother to resist as Celestia offered his cock up to her own sister. He even lifted his head from the table, cleared his throat, and spoke in his own trembling, slightly timid voice.

“It’s...It’s okay if you want to play with us, too.” He offered with a smile, just as Celestia let her hand stroke from his tip to his shaft, enough to make his hips gently lift from the table. He shuddered with glee, and as his eyes passed over the vice principal’s body he couldn’t help but imagine just what it would feel like inside of her. “I...I think I’d really like that, too.”

The two lovers had been interrupted, but they were hospitable within it. Celestia held Aero’s cock at the base, offering it to her little sister - a kind gesture she did not have to make. And Luna, still drifting somewhere in between shock, curiosity, and arousal, found herself stepping forward for the first time. Her knees were weak, her heart was racing, and despite every good sense inside of her she felt her hands moving to the belt of her dress pants.

It had been a while, after all, and Aero’s cock looked like one that was well worth the wait.

\---

Despite her hesitations, something inside of Luna was so eager to join in that she was kneeling on the kitchen table before she even fully managed to get her pants off. It took her a few quick shakes of a leg to finally dismiss the fabric to the floor below, and wedged in along with them was the thin fabric of her moistened panties. With her work shirt and blazer still on Luna crept up to join Aero and Celestia; the latter of which invited her sister over with a warm smile and open arms.

“Glad you’re ready to treat yourself a little, Luna.” Celestia beamed, and moved so that she was mounted right over Aero’s belly. She lowered herself down on the young man’s body such that he could feel her wet slit press against his flesh, and her hand still held his heavy length sticking straight up. When Luna swung a leg over Aero’s lap so she could enjoy the same pleasures as her sister, Celestia continued to hold it firm to make sure her sister could savor the moment. She watched with glee as Luna started to slink down, and her dark-skinned pussy pressed to the very tip of Aero’s thick, throbbing cock. As the clear mastermind of the tawdry threesome, Celestia giggled as she glanced over her shoulder to look at the young man still laying flat on the table. “Aero, you’d better not forget about me now that you’re getting to enjoy some slightly younger pussy!”

“I...I promise I won’t!” Aero whimpered, and rocked his hips in a building lust as he felt Luna start to descend. A little more than a week ago he was just a virgin, but now he was already experiencing the warm, wet grip of the second pussy to ever let him inside. Luna was slinking down his shaft inch by inch, taking it nice and slow as his member filled her out. Aero was left gripping the sides of the table with a white-knuckled grasp; his chest rapidly rising up and down as he struggled to keep his composure. It felt different from Celestia’s pussy but still overwhelmingly joyous, so much that he couldn’t help but to let his voice carry to the two sisters riding him. “V...Vice Principal Luna, you feel so...so good…”

“Our young friend knows how to appreciate an older woman’s pussy.” Celestia looked back to her sister and slinked her hands forward, taking Luna by the waist and pulling her near. She ignored any semblance of decency between herself and her closest relative, pressing her bare chest to Luna’s shirt and dropping their mouths sweetly close. As she whispered to Luna’s stunned features her warm breath cascaded over the other’s lips; helping to add an alluring assurance to the somewhat frightening moment. “I know how lonely you’ve been lately, Sister. I promise...you’re going to love this.”

“It already feels...feels wonderful.” Luna quivered in response, though it was clear that it took the younger woman a considerable amount of effort to find the words. She was still letting her lustiest instincts guide her, allowing the momentum of the moment to sweep her up. If she thought too much about what she was doing, she could’ve easily fainted. It was easier to focus instead on how good that young, enormous cock felt as it slowly stretched her pussy. Soon she bucked forward and claimed every inch of Aero inside of her, and as she rested on the boy’s hilt her hands moved forward to hold Celestia’s shoulders. Bracing herself, she took in several long, deep breaths, and finally offered a tiny whimper of helpless desire. “...Aero...you’re inside me…”

Nobody was more aware of that obvious fact than Aero himself, but it was the only thing Luna could manage in her aroused, bewildered state. Thankfully, her big sister Celestia was there to help. The older woman’s arms moved around her sister’s waist and she started to rock up and down while holding her; dragging Luna up to the point where Aero’s thick cock was nearly pulled from her pussy, only to shove her slowly back down. The first few thrusts of Aero’s cock into his vice principal was by Celestia’s own efforts, since both of the current lovers were otherwise stunned into a solid state. As Celestia continued with those motions her own pussy rubbed back and forth across Aero’s flat belly, leaving his flesh glistening with her arousal and coated in her heat.

Aero laid there with his length being fully embraced by Luna’s warm slit, his hips only able to rock forward to meet her after a few moments finally passed. The experience of his second pussy ever was just as thrilling as the first, and the mild mannered boy handled it with the same weight and worship that he handled Principal Celestia’s. This glorious older woman wasn’t just willing to have sex with him, she was eager to, and that was worth giving every bit of his effort. When he was able to pry his hands away from the edge of the table he moved them up to hold Luna’s waist, joined there with Celestia’s hands as they helped the vice principal ride him. He swallowed and shivered and did all he could to hang on; to keep himself hard and hold back from releasing no matter how much he wanted to.

Celestia continued to play the role of the mischievous woman in the middle, happy to see both Aero and her little sister so happy. She squeezed in closer and continued to ride Aero alongside Luna; rocking her hips up and down to keep kissing his belly with her wet, warm pussy. As she drew in close her lips moved to the edge of Luna’s ear, and she ducked her shoulder under her sister’s chin so Aero could see Luna’s face while she was fucked. In that content position Celestia started to whisper, and with even more sinful pleasure offered a few delicate kisses across her little sister’s ear, cheek, and throat.

“He’s a little shy at first, but just wait until he gets comfortable with you.” Celestia purred, and her hands crept from Luna’s waist to reach down to her sister’s bare, dark-skinned rump. She took two fistfuls of warm flesh within her hands, make Luna gasp and buck her hips forward from the action. While she double-grabbed her sister’s ass and helped her to fuck Aero all the harder, Celestia’s tone continued to dance across Luna’s goosebump-clad flesh. “Aero’s going to drive you crazy with his cock, Luna. It’s so good when you can finally let yourself go...when you throw all that worry aside and just let him fill you up…”

“Y-Yes...yes, it’s…” Luna looked over her sister’s shoulder to the face of the boy underneath her; framed in silver hair with such handsome young features. It was hard to imagine someone his age could be so well-endowed, and yet the proof of it filled her with every motion. “Oh, Celestia, this is...thank you for sharing with me…”

Celestia merely giggled, and her motions picked up to help her little sister fuck her student all the faster and harder. Luna had finally found the strength to move her hips as well, and together the two women worked to bring as much pleasure as they could to the boy underneath them. Luna held on to Celestia as she rode Aero’s cock, and her eyes remained transfixed on the face of the young man below, studying him and trying to wrap her head around the joy filling her. She was reckless that afternoon, and that same carefree nature continued as the three of them just kept going, grinding and thrusting and riding until finally, with a sudden gasp, Aero bucked his head back and pushed his lap up with one fierce, final thrust.

“Ahh…!” The boy’s cock started to throb within Luna’s pussy and his torrent of cum was suddenly unleashed. Luna gave an equally delighted cry as she convulsed against her sister’s body, only held in place by Celestia’s strength with her orgasm rocked through her. Both Luna and Aero were stunned and shuddering in their heated climaxes, though the coy Celestia could only imagine just what was going on below the surface. Aero’s eager little swimmers rushing up into Luna’s shivering folds, sweeping past her nectar and pleasure and gliding around those warm, pink walls. Just like she knew had already happened to her, Aero was breeding her sister in that heated moment, sending his cream to do its duty. Luna would be carrying that boy’s creampie only for a few moments, but she’d be carrying something else for many months longer. The thought of it made Celestia groan in delight as she kissed at her sister’s throat once more, and finally let her hands peel from Luna’s ass so she could find Aero’s and give them a little squeeze.

“Looks like you’ve got two girlfriends now, Aero.” Celestia purred to the boy underneath them, and licked her lips in aroused fashion. After all, the older sister still needed a creampie of her own. “Think you can handle dating two older women at the same time?”

Aero looked from Celestia’s alluring frame to Luna’s pretty features; still marked with sweat, still gasping, and still shuddering as cum oozed out of her pussy across Aero’s shaft. He would’ve had to be crazy to turn down such an offer, and his hands returned the squeeze to Celestia’s as he responded.

“You bet.” He offered in a short gasping breath, and steeled himself for what would come next. Having two sisters ready to ride his cock was a hell of an accomplishment for a boy of his age, and Celestia found herself beaming with a bit of pride at how far he had come in just a week or so. He was a fine boyfriend that had always left her drowning in satisfaction, and now that her sister was joining the fun she could stop feeling guilty for leaving her out. Sure, they’d have to be more careful - after all, that damned Cinch of Crystal Prep was always looking for dirt - but it was well worth the risk. Celestia moved a hand down to dust her fingers across Aero’s silver hair, and gently caress his cheek.

“...let’s go upstairs.” She murmured, and gently began to lift herself up from the kitchen table. “You’ve still got plenty of work to do, young man.”

A model student always put in as much extra credit as possible, and always tried to make as many teachers happy as he could. It just wasn’t always this much fun.

End of Chapter Two.


	3. A Cinch in the Armor

**Summary for the Chapter:**

> Hope you're in the mood for more student/teacher shenanigans, because Aero's back and he's seducing a whole new gal! This time, the vastly underappreciated Ms. Cinch. (I'll never get why more people don't like her! Or at least don't want to smuttify her properly!)

Mature Tastes  
A Cinch in the Armor  
-by Drace Domino

“You’re saying...you don’t want me around anymore?” Aero Ruinwing’s throat tightened as he said the words, emotion swelling up within him rather quickly. It sounded like he was being told particularly bad news, despite the fact that he was laying naked in bed with a gorgeous older woman on each arm. Vice Principal Luna was sleeping contently with her head in his lap and one hand gently holding his cock against her cheek, while Principal Celestia was merely pushing against him from the side, letting her full, mature breasts practically envelop his features. At the young man’s words of concern Celestia was quick to console him, smoothing one hand down the back of his hair while her other drifted across his bare chest, walking her fingers along his flesh in gentle fashion.

“That’s not what I’m say at all, silly boy.” She cooed, and squeezed a little closer against him. Even in that gentle motion she could feel cum leaking out of her very filled pussy; cream oozing from her hole with nearly every breath. They had just finished another marathon session of using Aero’s cock to great delight, and while Luna was clearly too tired for anything else, the principal was doing her best to be responsible. “It’s just that there are those who would...take issue with our relationship. Students and teachers don’t have this sort of romance very often, you know.”

“Well, who’s going to tell them?” Aero looked up, his face still clearly showing curiosity. He wasn’t quite as upset for the moment, thanks in part to Celestia’s hand at his hair, and Luna’s sweet sleep-fondling of his cock. “I promise I won’t! I wouldn’t want to ruin this!”

“Even if none of us ever say a word, people might find out.” Celestia cooed, and tapped her chin. “Besides...Luna and I have an enemy out there, and she’d love to get us into all sorts of trouble. Principal Cinch at Crystal Prep...we have a complicated history with her.”

The Friendship Games had been in the news. A stunning defeat for Crystal Prep - even though technically the thing had been a draw on account of magic. Still, the word around town was that Crystal Prep had been humiliated, and that was enough to make Cinch despite Celestia and Luna even more. Thankfully, the principal of Canterlot High had a plan in the works...and a secret weapon to unleash upon Principal Cinch.

“I’ve already filled out the transfer paperwork.” Celestia cooed, and finally allowed her hand to swing down to Aero’s cock. She pried his member away from her greedy sleeping sister’s fingers, and gave it a slow, sweet pump to make the young make flinch in his seat. With a giggle, the mature principal continued to stroke her young lover as she whispered. “You’ll be starting at Crystal Prep on Monday. And while you’re there...I’d like you to do something for me.”

“What’s that?” Aero asked again, and bit down on his bottom lip. This was...all happening very quickly. He didn’t want to transfer to a new school, but he was smart enough to see the wisdom in it. Principals Celestia and Luna could only call him out of classes so many times before people figured out that it wasn’t for anything school related, and in actuality he was fucking them both several times a day. As his member throbbed within Celestia’s grip, he gave the older woman a kind smile and even a thumbs up with a free hand. “I’ll do anything you want me to, Celestia. I love making you and Luna happy!”

“That’s wonderful to hear.” Celestia smiled, and quirked a brow as she began. Her hand tightened a little on his shaft, and her pumping quickened in pace as she explained her terms. “Now, if you’re a good boy and listen very carefully, when we’re done we’ll play a little game of ‘don’t wake Luna while I give you a blowjob.’” She purred, setting forth a very tempting reward. “Now...here’s what I want you to do…”

Aero merely leaned back and listened to the words of his mature lover, his length spasming joyfully in her grip and his heart racing at the closeness he shared with them both. Celestia and Luna were his girlfriends, breeding sluts, and his principals. He’d do anything Celestia asked of him, and as the older woman continued he realized that her request was both a bit scarier, and much more exciting than he ever would’ve guessed.

\---

It was one week later, Friday of his first week at Crystal Prep. It had been a long first week but Aero had been adjusting well enough; the students at his new private school were generally better behaved than the ones back at Canterlot High. (No one had filled the halls with confetti from a cannon, for example.) It was perhaps a bit dull and the other students were plenty conceited, but it was a pleasant enough place to learn.

...and as an added bonus, he was actually learning, since he wasn’t getting pulled away every two hours to satisfy the ravenous lusts of a couple of very, very horny MILFs. This week, he had saved all of his energy during school so he could do double duty as soon as he came home to the pair. Celestia and Luna were likely waiting in anticipation for him to come home that evening, probably wearing something sexy and revealing and eagerly pawing at each other in anticipation. Unfortunately, that night they’d be waiting a good bit longer...because Aero Ruinwing had been called to the principal’s office after school.

“So. Mr...Ruinwing.” Principal Cinch was scary, there was no other way of putting it. She had a stern face and never smiled that Aero had seen, and her reputation at Crystal Prep was one of dominance, aggression, and punishment. She was a harsh woman that demanded the very best from her students, and now...he was one of them. As the woman leaned back in her office chair, squaring her glasses on her face and folding one nylon-clad leg over the other, she let the uncomfortable silence hang in the room. Aero naturally squirmed back and forth in his seat, impatient and worried in the same breath. If she didn’t make this quick, he was going to miss the bus!

“Y...Yes, Principal Cinch?” He finally squeaked out when the older woman never finished her thought. He did his best to be respectful and pleasant, hoping to appeal to the woman’s disciplinarian side. Principal Cinch didn’t seem like the kind of woman you could win over with simple pleasantries. “What may I do for you today?”

“I’ve been watching you since you transferred from Canterlot High, Mr. Ruinwing.” Principal Cinch finally spoke again, standing to her feet and smoothing her hands across her outfit. Her sharp suit was finely pressed and straightened, streamlined to give her that presence of authority and poise. The woman somehow blended stern and sexy into a single package, and wrapped it in a level of unapproachable professionalism. “I would have paid close attention to any transfer from that school of...ruffians. I lost one of my best students to their ranks, and I’m very doubtful that Principal Celestia would send one of her favorites to me in return. I can only assume you’re a troublemaker at Canterlot High, and that your principals had simply had enough of you.”

She had no idea that neither Celestia or Luna could ever, ever have enough of him or the mammoth length he was hiding in his Crystal Prep uniform. Aero remained silent as Principal Cinch walked around to the front of the desk, every step patient and measured as she held her chin in her hand. Aero was still left squirming, though not necessarily form worry so much as...arousal. Being with Luna and Celestia had taught him a fine appreciation for older women that were firmly in charge, and Cinch had a presence that was downright exotic compared to either of them. Cold, unaffected, and calm were the opposite of the fondling lovefest that went on in their bedroom every night.

“I’ve paid...close attention to you. Very...close...attention.” Principal Cinch continued as she walked, taking her time as she made her way to the corners of her office. She strolled first to the windows where she peered outside the blinds, and then swiftly closed them with a tug on a cord. As the rattle of the blinds closing filled the room she made her way silently over towards the door, where she locked it with a single click as her gaze levelled on Aero once more. “And I’ve decided...you are indeed trouble, but not nearly the sort that I first thought.”

“I’m afraid I don’t understand, Principal Cinch.” Aero murmured, and blushed vibrantly at the woman’s words. Part of him wished he could hide the bulge that was clearly visible in his slacks; a noticeable length that was pressed hard against his thigh. He would’ve covered it with his jacket, but he was under gentle orders from Principal Celestia not to try hiding it. To simply...let nature take its course, as seemed to already be happening. “What kind of trouble am I?”

“Trouble for me, to be certain.” Principal Cinch continued, spinning on a heel and moving back towards Aero. This time she didn’t sit on her side of the desk, but rather moved to stand before him. Her rump rested on the edge of her desk and she folded her arms across her chest, as if pondering a very difficult riddle. Once more her eyes darted from top to bottom of her new transfer, taking particular note of that impressive bulge. And with a gentle grunt of what could only be surrender, she finally made a stern, decisive nod. “Yes...quite a bit of trouble for me.”

“I still...I’m sorry, Principal Cinch, I still don’t understand.” Aero didn’t want to lie to her; of course, but it was all a part of Celestia’s plan. He knew damn well just what she was talking about, and when the older woman’s hands lowered to the edge of her pencil skirt, Aero wasn’t particularly surprised. Principal Cinch sat up to the edge of the desk and lifted one leg to brace at the corner, fully exposing that underneath her skirt her pussy was eagerly waiting for him. No panties, and her nylons only travelled up to the middles of her thighs before attaching to a garter belt. As she exposed her smooth, slick pussy to her new transfer student, Principal Cinch slid a hand down to frame her pussy with her fingers and show the boy just how wet she was.

“Do you understand now, Mr. Ruinwing?” Principal Cinch finally asked with a lifted brow and a steady, teasing smirk. It was easily the closest thing Aero had ever seen to a smile on her face, and that was enough to make him feel all the happier. “Your mouth, boy. Put it to good use.”

“Y...Yes, ma’am!” Aero blurted out, a blush lining his features. He had to admit...when Celestia had first revealed her plan, he had his doubts. But with the taste of yet another mature pussy mere inches from his lips, it was clear the woman was a mastermind.

\---

A slow and satisfied smile crossed over Principal Cinch’s face as she allowed her heel to lift off the desk, her leg crossing over and folding across the opposite. Her skirt settled around her lap, and she gazed down at the tuft of silver hair sticking out from between her thighs. Her nylon-clad legs were sandwiching Aero’s head between them, leaving the young man with nowhere to look but to that tight, wet slit beckoning his attention. And Aero, using skills that he had learned in his past few weeks with the sisters, was more than happy to oblige this request.

His eyes were closed as he worked; his hands moving to slide underneath the sides of Cinch’s ass as he parted his lips. His tongue drifted forward and he enjoyed the taste of his third pussy ever; a different flavor than Celestia or Luna but still enchanting in its own way. The scent of this older woman’s arousal was intense, and Aero could already tell that for Principal Cinch...it’s been a long, long time. Just a few licks in, and she was already soaked to the core, and every lick just seemed to make her all the more wet. While Aero worked his tongue back and forth across her sensitive hood Principal Cinch was busying herself with removing her clothing; slipping out of her blazer and setting it aside and then moving her fingers to the first button of her shirt. Unfortunately, the young man was so damned talented with his tongue that she didn’t get further than the second button before the older woman was desperately grabbing the edge of her desk.

“G...gah! That...that’s so…” She groaned, tightening her thighs and rubbing them back and forth across the boy’s cheeks. A heavy blush crossed her features and she looked uncharacteristically taken off guard, clearly not expecting to find this much skill working between her thighs. She was planning on taking her time in teaching a young man how to eat mature pussy, and didn’t count on him bringing expert skills to the occasion! One of her hands left the edge of her desk and slipped into Aero’s silver hair, tightening her fingers within the locks and pulling him forward a little more. “Just...just like that, Mr. Ruinwing! My...my, you’re a natural!”

He was, but that didn’t mean he didn’t have a ton of experience to back up that skill.

While Aero slurped and suckled against his new principal’s pussy, it was natural that the boy’s member was responding in eager fashion. His cock had already been stiff from having Cinch pace around in her bossy fashion, but now that he had those nylons against his cheeks and the taste of her pussy across his tongue, it felt downright uncomfortable to keep his cock in place. One hand slid away from Cinch’s ass so he could hurriedly reach down to his belt, whipping it free and unfastening the top button of his pants. He needed relief; or at the very least, a chance to let his cock stand free without the restrictive fabric holding it in place.

Principal Cinch couldn’t see Aero’s cock from her position; her legs crossing nicely around the young man’s face, but she could still hear him unleash it. A soft chuckle rose from her throat and she pawed her fingers again through his hair, her words marked with a steady groan of pleasure that poured from her lips with a sultry, mature delight.

“Ohh, so eager, Mr. Ruinwing.” She cooed, and bit briefly down on her bottom lip. The lucky woman had no idea just what was in store for her, otherwise she very likely would’ve foregone his mouth and launched right into the main event. “If you’re playing with yourself down there, I suggest you stop. I’ll be...rather upset if you’re not in a proper state to fuck me when you’re done here.”

Aero was a bit too sweet to think as much of her, but he could certainly imagine Principal Celestia taking mischievous delight at just how...naive Principal Cinch was. It was more than just a little cute.

Aero’s eyes finally lifted up from his work, and he stared along the body of the sophisticated older woman - at least as much as he was able, considering his lips were still wrapped around her hood and his tongue so eagerly lashing her clit. With her first two buttons undone Aero could just barely see the outline of Principal Cinch’s bra, and it was a far cry from the sexy affairs that Celestia and Luna had started to wear for him every night. Boring and plain, as he imagined Cinch’s panties were before she had snuck them off before their after school meeting. It was the undergarment of a woman that didn’t get out much and didn’t see a great deal of pleasure, and that fact alone was enough to make Aero work all the harder. He gazed up at his teacher’s gasping face while his tongue worked overtime across her pussy, drinking in every bit of nectar he could manage and savoring the glorious taste. Underneath he was indeed fondling his shaft, but only barely - just enough to keep himself as hard as possible for the moment that Principal Cinch demanded it.

Celestia might have sent him there in order to seduce Cinch and take away any leverage the woman could have over her, but in that moment Aero had firmly decided the true mission parameters for that evening were to make Principal Cinch happy, and ensure that she received the attention she so desperately craved. She deserved it, after all. She was a talented educator and a beautiful woman in her own slightly stern right, and yet all of the other students were so...cruel to her. Constantly whispering behind her back, trying to subtly subvert her orders, even talking about how great it would be if Dean Cadance became the principal.

Well, the Shadowbolts could talk about Principal Cinch all they wanted. Aero was going to use his mouth to a more meaningful purpose.

“Hahh...hah...y-yes, there...right there…” Principal Cinch’s whimpering was intensifying as time went on, and she no longer had the tenacity of spirit to tease the young man trapped between her thighs. With one hand fiercely grasping his hair and the other clenched around the desk’s edge, she was rocking wildly back and forth and grinding her hot, wet slit to his face in more frequent and rapid motions. Thanks to his training with the sisters Aero knew that she was near her peak, and as soon as it began he took steps to make it as wonderful as he could.

Principal Cinch’s orgasmic cry filled the office and even down through the empty hall, filled with rich lust and heavy desire that only the passions of a pent up woman could muster. When her orgasm began Aero quickly let his hands flip up, pushing his palms behind her knees and prying her thighs away from the sides of his face. He lifted her legs as best as he was able while she started to spasm and gasp, eventually to the point that his teacher was sitting with her legs spread eagle at the edge of the desk. His tongue curled and danced across her clit just as Celestia and Luna enjoyed, and when the squirt of her nectar came he gladly let it batter his cheeks without a single thought of recoil. In fact, he seemed to relish in it. By the time Principal Cinch was done with what was quite likely her first orgasm with another person in a very long time, she looked down to see the face of a handsome young man whose cheeks were wet with squirt and glistening across a heavy blush. And unlike the reaction some other teenage boys might give her, Aero was working on moments of tender aftercare. Kissing along her lips while being careful to avoid the post-orgasmic sensitivty of her clit, or even biting down gently at the inside of her thighs to give her tiny, pinching pleasures. When he finally looked back up to the older woman he saw the face of a stunned principal, the color drained from her cheeks and her glasses slightly askew on her face.

“Did...did I do well?” He asked, making sure his words were marked with proper grammar. Principal Cinch seemed like a stickler for it. “You look like something’s wrong, Principal Cinch.”

“Oh...oh my...you sweet boy.” Principal Cinch merely swallowed in response, and her heels started to leave the air. Soon she was standing once more, though still heavily leaning back against the desk to support her trembling frame. “You’re...quite talented. And very considerate. And you’re...you’re…” Her eyes went even wider, and she took the time to adjust her glasses just to make sure she was seeing things clearly. “...you’re enormous.”

Aero merely looked down at his lap and the stiff cock sticking up from it, marked with a dot of precum and desperately bidding for the older woman’s attention. In his typical sweet fashion Aero tucked his hands into his pockets and blushed, looking up at Principal Cinch as he lightly nubbled on his bottom lip.

“Heh...t-thank you, Principal Cinch.” He murmured. “Would you like me to...to…” There were many ways he could’ve said it. He could’ve asked if Principal Cinch wanted him to fuck her, which was most likely what Celestia would’ve wanted. He could’ve asked if she wanted to have sex. But instead, in that moment Aero felt like his choice of words was very, very important...and there were words that Principal Cinch needed to hear. “...would you like me to make love to you, Principal Cinch?”

He could tell instantly by the look in the older woman’s eyes that he had chosen wisely, and that a layer of her rocky exterior had melted away right then and there.

“I...I would very much like that, young man.” Principal Cinch swallowed nervously, and gave a gentle nod. “Let’s...let’s begin.”

\---

Just this once, Aero knew better than Principal Celestia. He wasn’t a boy that would question the older woman’s judgement all too often, and he certainly didn’t plan on making a habit of it, but once he was alone with Principal Cinch it became very clear the stern ruler of Crystal Prep was far more than she appeared. Now, with the many inches of his cock wedged tightly within her entrance, he could see that much in her eyes even more clearly. With Aero seated in the principal’s office chair and Cinch straddling his lap, he could hold his hands to her waist and help guide her down until every bit of him filled her. And all the while, he did his best to make the lonely older woman feel welcomed and warm within his company.

“You’re so beautiful, Principal Cinch…” He whispered honestly, leaning in and pressing a few faint kisses across her throat. She was more sensitive than Luna or Celestia, likely thanks to her lonely nights. When she was finally resting fully in his lap and every inch of his cock was stretching her entrance, Aero nuzzled her ear with the tip of his nose and gave a tiny laugh. “...okay, that’s all of it. Do you like it?”

It might’ve looked a bit salacious, maybe even preposterous, her larger frame kneeling in the younger boy’s lap, but there was nothing small about the meat that was filling her. With a tiny gasp Principal Cinch looked fondly to Aero, adjusting her glasses before bracing her hands on both of his shoulders. Her smile was warm and doting, a smile that she likely offered no other student during her time at Crystal Prep.

“I adore it. And you too, Mr. Ruinwing.” Principal Cinch cooed, just as she slid a hand to the back of the young man’s head and pulled him in for a deep, intimate kiss. Her lips pressed firmly to Aero’s own and her tongue quickly sought his out, wrestling playfully with it as the two became accustomed to each other’s flavor. Naturally, the taste of Cinch’s pussy played within their kiss, but it only seemed to spurn the older woman forward and encourage her to begin rocking her hips. The office chair squeaked underneath them as Principal Cinch started to grind back and forth, her hips lifting a few inches before slowly descending right back down. She didn’t seem interested in fucking Aero with quick and reckless depravity - and why should she? For a woman that had been forced to go without for so long, she deserved the chance to savor this moment.

Aero was more than happy to oblige. His hands moved from Cinch’s waist to her back as he held her close, feeling her ample bust press to his own rapidly rising chest. His member was firmly enlodged within the tight, wet entrance of his third older lover, and every inch of it was being thoroughly worshipped by Cinch’s passionate nether embrace. Her walls squeezed upon his shaft every time she started to pull back up, and when she descended she always made sure to push down just a little bit extra than gravity would’ve allowed, making sure that the contact was as deep as she could muster. The boy’s cock was an impressive fit inside of her, and every time she rolled back and forth there was a slow, wet sound that spoke of just how firm a grip she was. It didn’t take long for Aero’s hands to drift around to Cinch’s backside and take two gentle grasps of her rear, his hands resting underneath the hem of her skirt and his fingers drawing tight on her flesh just above where her nylons began. He did his best to help her out with her motions, but it was still quite clear she was doing most of the work herself. All Aero had to do was sit there and let his principal ride him, wrestling her tongue with his own and melt joyfully into his seat.

“Mmm...Mr. Ruinwing…” Principal Cinch murmured within the kiss, even though she didn’t seem like she felt particularly like chatting. Her mouth pulled up from his every few seconds to whimper sweet words of no consequence, mostly gentle beggings for more or praising just how well he was filling her. She kept a hand in his hair while the other slipped underneath his shirt, fingers passing over the hairless frame in appreciative fashion. “...so...wonderful...I needed this so much…”

It was clear that she wasn’t lying, and Aero was simply happy that he could be the one to give it to her. It wasn’t enough for the boy to merely fuck Principal Cinch that evening, he wanted to make sure that when they said goodnight that she knew she was special. That she was beautiful. That she was just as worthwhile as any other woman. His kisses, his gasps, even the gentle thrusting of his hips did their best to encourage that thought within her. Whether or not she got the message would remain to be seen, but everything he was doing still managed to push Cinch to a very particular moment - a moment of rich, passionate climax that echoed through every muscle of her body.

It was a climax unlike Aero had seen yet. Far from Celestia and Luna’s screaming and spasming climaxes, far even from Principal Cinch’s squirt from earlier. She tensed up, she gripped him fiercely about his shoulder and hair, and her body froze perfectly in place with every muscle locking at the exact same time. Her lips broke from his as she squeaked, even sobbed a few gulps of desperate noise, and the grip of her pussy became far, far too much for Aero to endure. As Principal Cinch had an intense orgasm while riding the young man’s cock, he was utterly unable to stop from releasing inside of her.

His mouth moved to claim Cinch’s in another kiss when the moment came, as if it would distract her from the fact he failed to pull out. His cock began to release a torrent of little swimmers right into the older woman, and considering how deep his cock went within her they didn’t have far to go in order to seek out her womb. As Aero violently trembled underneath Principal Cinch’s weight he could feel his member throb with purpose and determination, and even if it wasn’t his original intent his cock was going to see to it that yet another older woman became pregnant under his watch. As his cream flooded her entrance he could just imagine how his seed was swarming around one of Principal Cinch’s eggs, each one eager and ready to do the job they were created for. Principal Cinch was most certainly bred that late afternoon after classes, and by the time she recovered from her orgasm she was practically glowing with satisfaction. If she had the same concerns about getting pregnant she certainly didn’t show it, and instead smoothed her hand down the back of the boy’s head before leaning down and giving him a tender kiss.

“Thank you, Mr. Ruinwing.” She cooed, and continued to rest there atop his stiff, still-spasming cock. “Thank you so much for a...surprisingly lovely evening.”

Aero merely smiled at his new principal, and wrapped his arms around her waist to give her a big, tremendous hug. HIs face pressed against her breasts and he closed his eyes within the embrace, naturally assuming that a good quality hug was exactly what a woman like her needed. Sure enough he was right again, and soon Cinch’s arms had returned around him in an embrace that was just as warm, inviting, and caring.

There was only one thing that Aero was wrong about that evening - and that was the intent of the woman that had sent him there. The entire time with Principal Cinch, including the fuck session he had with her atop the woman’s desk, he naturally assumed that Celestia had sent him there in order to somehow subvert the older woman. Or at the very least, that she didn’t intend on him satisfying a part of her that went deeper than pleasures of the flesh.

But in reality, far across town Celestia was resting comfortably on the couch with Luna, content that somewhere her dear Aero was doing something that came very naturally to him. Making the lives of older women better through his kindness and his compassion.

And his cock, of course.

End of Chapter Three.


	4. Sweet Setup

**Summary for the Chapter:**

> It's Cadance's turn! How many MILFs this boy gonna collect, anyway?!

Mature Tastes  
Sweet Setup  
-by Drace Domino

“You wanted to see me, Principal Cinch?” Cadance’s voice was soft and sweet as she opened the door to her boss and mentor’s office, her brow gently knit and her cute features looking forward in a slightly nervous fashion. She had to admit - things had been awkward between her and the older woman ever since some of Abacus’ bolder moves against Canterlot High. Competition with the public school had driven Principal Cinch to the point of aggressive behavior, and Cadance couldn’t always say that she agreed with the older woman’s actions. Still...if there was a woman that had been like a second mother to her, it would be Cinch. Stern and sour as she was, Cadance could never deny everything that Principal Cinch had taught her. And so when she called, Cadance answered.

Even if it was at the school after hours, and even if there was an unexpected guest in the office; the new transfer student.

“Oh! Uh...hello, Aero.” Cadance smiled at the young silver-haired boy, and even gave him a tiny wave. As she stepped into the room Cadance took the time to survey everything; Principal Cinch was behind her desk with hands folded just under her chin, looking like a stoic gargoyle that couldn’t be moved except for the most tremendous of forces. And Aero sat right across from her desk in his Crystal Prep uniform, small and slender and handsome for a boy his age. He had a book resting in his lap, and though he returned Cadance’s smile his cheeks were blushing tremendously - so much so that it didn’t seem like he could really respond to the older woman’s greeting. What had the boy looking so shy and timid?!

“Dean Cadance. Please, sit.” Principal Cinch gestured to the other chair beside Aero, and continued before Cadance had even pressed her rump to the cushion. “I called you here this evening for a matter of intense importance. Something that requires critical attention.”

“Oh…? Well, then in that case, I’m all ears!” Cadance’s eyes had opened wide as she smoothed her hands down her skirt; keeping it nice and neat and polite in the presence of young Aero. She even calmly moved a hand up to sweep her purple, pink, and cream hair back, tucking a few pretty strands behind her ear. Once more she looked a bit concerned about the matter at hand, and looked from Aero to Cinch and then back again. “Is...is everything okay with our new student? He’s not in any danger or anything, is he? Is he being bullied?”

“Oh no, not at all, ma’am!” Aero finally found the courage to speak up, his book resting on his lap and staying firmly in place. He fought through his embarrassment as he addressed the newcomer, blushing through it all. “Everything at Crystal Prep has been really nic--well, everyone at Crystal Prep has been very poli---uh…” He bit his lips together as he tried to think of a correction, before finally blurting out. “Principal Cinch is really nice to me!”

She really was. Even though it had only been a day since Aero had fucked her in her office, it was hard to deny that she had been anything but kind, doting, and accommodating to him. Even if the rest of the students were...well...a bit bitchy, to say the least.

“Oh! Well, that’s good to hear.” Cadance beamed, and even stretched a hand out to pat Aero’s shoulder in sweet, fond fashion. “So...what is it we can do for you, Mr. Ruinwing? Is there something that’s making you unhappy?”

“Aero?” Principal Cinch spoke up, leaning slowly back within her chair and folding an elegant, nylon-clad leg across the other’s knee. She unfolded her fingers to gesture to the young man in silent instruction. “...show her.”

With trembling hands, Aero pulled back the book he was holding over his lap...and revealed the biggest cock Cadance had ever seen. The pink-skinned girl’s eyes snapped open wide as she saw it, and her pupils tracked its movements as it slowly rose from his lap to fully display its prominence. Thick. Long. Glistening with a dot of precum at the tip...and most notably? Lipstick marks in a kiss pattern on the side - the same rich, deep crimson of Principal Cinch’s chosen color.

Cadance clearly had plenty of questions, but thankfully Principal Cinch was there to answer them all. After all, it was what she was there for - to help her dean along, to help her figure out the trickiest of problems. Problems like...what to do when one of your young students was packing a cock that was simply too tempting to resist.

“Dean Cadance, last night Mr. Ruinwing fucked me right here in the office.” She announced simply, quirking a brow and nibbling on her bottom lip. She took a deep breath and let her gaze drift to Aero’s shaft, as if she could only barely resist the urge to lunge forward and keep smearing her lipstick all over it. “It was the best sex I’ve ever had. I’m still wet thinking about it. And this morning...would you like to know what he told me?”

Dean Cadance, the color draining from her pale pink cheeks, didn’t even look away from Aero’s dick as she squeaked out a tiny whisper of affirmation. She wasn’t sure anything that Principal Cinch could say would put things into perspective...but she was willing to listen.

“Tell her, Aero.” Principal Cinch cooed, and drew in another long, excited breath. “I enjoy hearing the words from your lips.”

The subject of all the attention, the sweet young man fidgeting in his seat, merely nodded. Aero didn’t even have to touch his cock to keep it stiff and hard; it simply kept jutting up from his lap demanding their gaze. His hands idly fidgeted with each other and he just kept blushing, and when he finally spoke his tone was certainly shy. Not ashamed...but shy. It was a strange thing to admit.

“Uh...I...I have sex with Principal Celestia and Vice Principal Luna of Canterlot High. A lot.” Those words were the only thing that could draw Cadance’s gaze from his length and up to his eyes, where she stared with the same disbelief. “I didn’t tell Principal Cinch about it last night, and I...kind of felt bad about it. I like Principal Cinch a lot, and I really had a lot of fun with her yesterday.”

As he spoke, Principal Cinch finally rose up from her seat, only to reveal that behind the desk, she hadn’t been wearing her skirt. Her full business blazer and blouse were still wrapped around her body, but below the waist she wore nothing but heels and thigh high nylons connected to a lacy, sexy garter belt. It was the first time that Cadance had ever seen the older woman’s pussy, and even then she was only able to lay eyes on it when Cinch walked all the way around the desk and stood just to the side of Aero’s seat. She slowly slinked one leg onto the armrest and let one hand drift into his silver hair, the other lowering to grasp his throbbing cock in surprisingly delicate fingers. There, fondling him on both fronts, she finally spoke to her student turned dean with purpose in her tone.

“It would seem like Celestia and Luna enjoy Aero’s company quite a bit.” She continued, smoothly and slowly as if it was any of Cadance’s business. “This morning before coming to class at Crystal Prep, they even sucked him off. And Aero dear...tell her what else.”

“Uh...Principal Cinch, I don’t know if I sho-” He gave a sudden gasp and a rock of his hips that lifted his ass up from the seat, trying his best to grind forward into Principal Cinch’s grip. The shockingly sensual older woman with the wireframe glasses and stern glare had squeezed his cock in just the right way, playing his young member like an instrument she had practiced for years. When Aero melted back into the seat his blush was tremendous, and a line of precum was oozing out of his tip and down along Cinch’s fingers. Once more he turned to Cadance, and offered his voice up in soft, timid fashion. “They’re...they’re almost definitely pregnant. I mean, we...we do it so much, and Principal Celestia never lets me wear a condom, and...and…”

“And it turns out our young Mr. Ruinwing is quite the stud.” Principal Cinch chirped up, releasing her grip on his length and drawing her hand slowly up to her face. Her tongue rolled forward and she kept eye contact with Cadance as she let her tongue slither forward, collecting the gooey, tasty precum from her finger and greedily swallowing it down. “As you know, my feelings about the sisters that run Canterlot High are...complicated, to say the least. But I was thinking, Dean Cadance...wouldn’t it be lovely if we had something in common with them?”

And there was the key word: we. Dean Cadance blinked as if she was suddenly snapped back to reality, and she looked between the two several times as her throat tightened and her heart raced. She once more slid her hands down her skirt as if straightening it would make the madness ebb away from her; as if it would quell the excitement that had been building inside of her against all reason and thought. Cadance’s voice was trembling by the time she spoke up again, though she already knew the answer to her questions.

“You...want him to get me pregnant, too?” She asked of her employer, her mentor, her second mother. Immediately after she looked to Aero, her voice ringing with disbelief. “And...and you? You want to get another woman old enough to be your mother pregnant?!” She was perhaps not quite that much older than him - especially not compared to Celestia or Cinch, but the premise was the same. She was a teacher! An educator! And he...he was a student with sweet mannerisms, handsome and youthful features, and a cock that was making it very difficult for her to resist.

And in answer to her questions, Aero and Principal Cinch were of a common mind and a common answer. They both nodded, and spoke in a short, simple affirmative.

“Yes.” They spoke in unison. Yes - they wanted Cadance knocked up, just like the others.

***

Aero’s and Cadance’s clothes both laid in a tiny pile together; one that Cadance was using as a pillow as she laid flat on the floor of Principal Cinch’s office. The sweet dean was wearing a vibrant blush that started at her cheeks and travelled down into her chest, giving her soft pink skin tone an enticing new glow as she was laid spread and displayed for Aero. Both she and the young man had been stripped bare mostly by the actions of Principal Cinch; the older, stern woman was in no mood to be the only one showing herself off, and Cadance still rather stunned into delighted complacency. Indeed, every time she looked at Aero she found herself gasping in excitement, her nethers pulsing with heat and arousal and her thighs becoming slick with nectar. Though she was still quite a bit overwhelmed with everything she had learned, it was quite obvious that she was on board with Principal Cinch and Aero’s desires.

And now, as Cadance laid flat on her back and Aero knelt before her, Principal Cinch was still there behind the young man as a guiding force. He definitely didn’t need anyone telling him what to do when it came to pleasing a woman, and yet still as she pressed her half-dressed body against his from behind it only made his cock throb a little harder. Cinch was ravenous even though she wasn’t the one about to be fucked; pawing her hands up and down Aero’s smooth, flat chest and letting her hands lower to grasp his hips or slip forward and lightly fondle his balls. She stood a full head higher than Aero and so it was no problem for her to see every inch of Cadance from her position, and as she spoke her eyes traced up and down the younger woman’s body as if judging whether or not she was good enough to please Aero’s dick.

“Are you ready, Cadance?” Principal Cinch asked, in a tone that made it perfectly clear she didn’t care whether or not Cadance said yes. One of her hands moved to the base of Aero’s cock, and as she squeezed him the young man whimpered and rocked into her grip. He was so gentle and sweet that he even nuzzled against her in response, tilting his head up to brush it back and forth across his principal’s throat. Cinch had no idea whether or not he was this affectionate with Celestia, but in the moment she didn’t care. All she wanted right then and there was to share in a fragment of the joy Celestia and Luna had - the experience of sharing a really wonderful, hot young cock with another woman.

“I...I’m ready, Principal Cinch.” Cadance whispered, and slowly started to spread her thighs to show herself off. In her naked state Aero could appreciate a body that most of the boys at Crystal Prep had lusted for at some time or another; Dean Cadance had large, round, wonderful breasts with large nipples that were clearly showing her joy. A tiny and trim patch of hair was sitting atop folds nearly the same color as the rest of her, the fur purple with two stripes of pink and cream just like the gorgeous hair hanging from her head. Aero’s cock was suddenly lifted up and slapped down once more with authority by Principal Cinch’s motions - his cocktip bouncing off of Cadance’s belly as the older woman teased her younger counterpart. Cadance merely gasped and trembled as she looked down at Aero’s length and imagined just how deep it would go inside of her, while the young man in the middle was left listening to Cinch’s voice. She pulled her fingers through his silver hair, cradled his head at her breasts, and cooed sweetly to him as she slid his cock from side to side, rubbing it back and forth across Cadance’s lap. “I hope you’re happy with yourself, young man.” She half-teased him, a surprisingly lighthearted tone ringing in her voice. “...just look how horny you’ve made your dean. I do hope you’re planning on...helping her.”

And with that, no matter what Aero said in response, Principal Cinch pushed down on his length and started to help him inside. Aero’s eyes shot open and he practically melted in that instant; leaning back fully against Cinch’s embrace and spreading his knees further apart to help his position. Cadance’s legs were spreading more and more and he lifted his hands underneath her knees, slowly pulling them up with every ounce of strength in his trembling arms. When he finally had them up in the air they looped not over Aero’s shoulders but Principal Cinch’s, further locking in the older woman’s role in the lovemaking that was about to happen. Aero’s heart was racing and his young passions were flaring intensely; this was every bit as intense as anything he had done with Celestia and Luna! He could feel his cock throb within the firm but loving grasp of Principal Cinch, feel his cockhead squeezed by the warm, inviting entrance of Dean Cadance, and all around him he was bathed in the scent of two very different, yet very appealing women. Dean Cadance; sweet, demure, gentle, tender. And Principal Cinch; stern, stoic, demanding, and critical.

And he knew in that moment as his cock slipped deeper and deeper into Cadance, that they both utterly adored him. It hadn’t taken much to win Cadance over; much like Principal Cinch she was practically smitten the second Aero’s length slipped inside of her and she was subject to the full weight of the boy’s charms. And as the rest of his inches flowed into the warm entrance of the older woman, filling her out and stretching her folds, she moved her hands up and above his shoulders to pull him near. With Principal Cinch still holding up Cadance’s legs, the younger two drew closer and Aero found his chest to Cadance’s own, their mouths drifting close.

“Yes...yes…” Principal Cinch whispered, her thighs glazed with the aroused juice of her own heated joy. Seeing Aero fuck the younger, sweeter woman was nearly as exciting as getting his cock for herself...though she certainly expected to get some before he left that evening. Like Aero’s perpetual shoulder devil she whispered from the back, encouraging the two as they started to kiss and Aero’s hips began to rock. “...fuck her...fill her up, Mr. Ruinwing...just like me…”

Cadance’s arms had locked around Aero’s shoulders, and as soon as they started to kiss he could tell that her passions were far from timid. Her tongue was a writhing and wriggling handful; slipping eagerly up and around his as she drew in long, savoring tastes of the young man’s kiss. Aero’s mouth was filled with the sweet taste of his dean just as his cock was enveloped in her amazing grip, and all the while he remained in that missionary position with Principal Cinch’s help. The older woman’s shoulders were occupied by Cadance’s calves and yet her hands were still on Aero’s waist to help; holding him steady, giving him a little nudge when he needed to fuck a bit harder, and on more than one occasion slipping down to fondle his balls in the slower moments.

Aero was a lucky boy indeed, having acquired the affections of both Principal Cinch and Dean Cadance - and that wasn’t even touching upon the two ludicrously hot, horny older women still waiting at home for him. Cadance grasped at him and kissed him as passionately as a bride would on her wedding night, tongue wiggling back and forth, grappling his own, and never truly letting it escape. Her walls clenched and squeezed his cock in a slow and steady attempt to milk it, though they were far from that moment of glorious release. After all, Aero had only just barely based himself inside of her...and there was still so much more fun for them to have.

Aero and Cadance seemed content to just kiss desperately and deeply while he slowly fucked her in the missionary position, but Principal Cinch wasn’t one to stand around so idly. With her intention of making the show before her a bit more exciting, she crept closer still and once more pressed her breasts to the young boy’s back. She leaned forward as her hands tightened to Aero’s waist and her mouth moved to the edge of his ear, and she could feel him tremble as her tongue took a slow, sweet lick just before a tender whisper.

“Let me help you fuck her, Aero.” She cooed, just as she started to rock along with the young man’s body. “...let me help you knock up your dean.”

And Aero, wanting nothing more in that moment than to do just that, was happy for her help. He broke the kiss between himself and Cadance and let the dean’s head rest back on the makeshift pillow; a combination of her bra and panties and Aero’s school clothes. Sure enough, he’d be wearing her scent home where Celestia and Luna would most certainly notice it. He didn’t have time to think about that moment; however, because Principal Cinch was already beginning to put her effort behind it.

“P...Principal Cinch...she’s so tight…” Aero whimpered as he fell back against her again, once more his head resting between the older woman’s breasts through the fabric of her blouse. His hips were already going faster, though only half the energy was his own. The other half was Principal Cinch keeping her body practically sealed to his from behind, letting her momentum and her effort help to lunge him forward in harder and harder strokes. The sound of his cock delving into Cadance’s wet, raw pussy was the only noise between them outside of their gasping and Aero’s gentle, hungry voice. “...t-thank you...for helping…”

“You’re welcome. Such a sweet young boy!” Principal Cinch merely cooed, threaded her fingers through Aero’s hair, and gave him a kiss on his increasingly sweat-lind forehead. That moment of tenderness was short lived; however, because once more she started to rock forward with eagerness and effort. She let one of her arms fully wrap around Aero’s slender waist as she squished him against her, and her glasses slid down to the tip of her nose as she gazed down at Cadance’s flawless figure. Pink breasts bouncing back and forth, eyes closed within a fit of passion, and that same dark blush making her practically glow. Principal Cinch’s voice slipped forward once more, hissing at the edge of Aero’s ear as they put everything they had into it. “Fuck her...keep at it...just like that…” She groaned, and Aero could feel her outright quake against him. “Ohh, I can’t wait until you let me clean her pussy off your cock, Mr. Ruinwing!”

Principal Cinch’s arm remained tight and firm around Aero’s waist, while her free hand went even lower. It even snaked behind him so she wouldn’t get in the way of Cadance’s fun, and her gentle fingers cupped the boy’s sack to keep fondling him throughout it. Slippery and slick - no doubt from Cadance’s squirt, his little pouch rested neatly in her hand and she treated it every bit as precious as it was. With her voice slipping away Principal Cinch found her mouth now moving up and down the back of Aero’s throat, kissing him hot and hungry and even letting her lips linger on his flesh and suckle until she rewarded him with a hickey. Something for Celestia and Luna to see - the equivalent of sending a peace treaty to them. If the heads of both their schools could enjoy fucking this boy so very much, then maybe they could get along?

Aero merely shuddered underneath Cinch’s affections as he kept pushing back and forth, all the while assisted by the older woman. He was naturally fully able to fuck and please plenty of older women with his own might, but keeping Cinch so close made things all the more intimate between the three of them. Even though he knew so little about Cadance, having Principal Cinch at his back made him comfortable and confident as his cock rammed in and out of her sopping wet entrance. And all the while as he claimed her, the boy gazed down at Cadance’s pretty features, admiring just how lovely she was.

“Ohh...ohh yes…” The words weren’t spoken so much as breathed past Cadance’s lips, only barely audible as she let her fingers slip from Aero’s shoulders to his silver hair. She let them dance through the locks as her hips thrust back into the young man’s lap with every push, and her toes curled in excitement as wave after wave of pleasure pushed through her. She even let one of her hands leave Aero’s hair and drift seamlessly into Principal Cinch’s, silently thanking her mentor for introducing her to the dick of the young man. She’d probably have to get comfortable being far more intimate with the older woman soon - the way things were looking, they’d be spending a lot of moments like this together soon! Cadance’s lovely pink breasts kept dancing and her sweat-licked body glowed with a blush as she spoke up once more, her voice hitching within her throat and sounding even more like a desperate gasp croaked from a body struggling to keep its composure. “...Aero...Aero, I’m going to...to…”

“M-Me too, Dean Cadance…!” Aero nodded eagerly, and as soon as he confirmed it Principal Cinch helped him to fuck even faster. Together the two slammed their hips back and forth in perfect tandem, and the wet noise of flesh clashing to flesh filled the principal’s office from wall to wall. “Are you...are you sure you...you want me to-”

“Yes, yes, cum inside of me!” Cadance begged desperately, going full circle from the shock she wore on her face when Principal Cinch had first proposed it. Her walls tightened around Aero’s cock as she let her fingers lock to his hair, yanking his face down so that they might share yet another wet, affectionate kiss. When their lips were but an inch away from one another she offered him another sweet whisper, one that was easily enough to push the boy into the throes of bliss that were already rushing against him. “...fill me up, Aero…! I want to have your baby, too!”

With that her mouth pressed to Aero’s own in a bold fashion, and once more she showed that her kisses were dominant, hungry, and demanding. As soon as the boy tasted the older woman again and felt her tongue wrestle his own to the roof of his mouth, as soon as he felt her hands slide to his shoulders and her nails dig in against his flesh, it was quite simply too much for him to endure. He gave a deep moan from his core as his climax finally arrived, and in that same moment Principal Cinch’s hands locked around Cadance’s ankles and pulled the younger woman as hard as she could while thrusting her body forward. It made sure that Cadance was fucked down to the hilt and beyond, that Aero’s cock was every bit as deep as the combined strength of three people could manage. Both Cadance and Aero shook almost violently within their shared climax, and if Cinch was still fondling her boy lover’s balls, she no doubt would’ve felt them pulsing with cum.

Aero’s length spasmed, twitched, flailed against the older woman’s walls as his tip unleashed a torrent of cream straight against the thin layer of the older woman’s uterus. Wiggling swimmers pushed forward fast and ready, and in a few moments they’d be piercing, penetrating, occupying parts within her that would ensure that just like all the others she’d soon be future mother. Celestia and Luna were already bred and it was certain that if Cinch wasn’t already, she soon would be. And as Aero’s dick continued to release wave after wave of creamy warm white into Cadance’s entrance and more of his nectar battered against the thin wall only barely able to stem the tide, the boy knew that he was about to father yet another child to yet another woman. How many older women could one boy knock up?! It didn’t seem like there was a limit, and they all seemed equally enthusiastic about getting fucked and filled with his cum.

In the aftermath, once more Aero’s head flopped back into the embrace of Principal Cinch’s breasts, and the older woman cradled him close as she let her hands go to work. She teased the fingers of one down Aero’s sensitive belly as she let her other grasp his cock at the hilt, gently tugging it away from Cadance’s pussy and pulling it out of her sensitive folds. The pink skinned girl gasped as his member flopped free and she felt cum start to leak out of her nethers, but she knew that he had already filled her with more than enough to get the job done. From there, Cadance fondled Aero’s slippery shaft in a particularly soft grip, just as her head lowered and pressed a tiny kiss to the boy’s brow.

“...you still have some for me, right, Mr. Ruinwing?” She asked, though in a large reversal of her usual tone sounded more understanding and sweet. Even if the boy was too tired to please her afterwards, she’d understand. ...even though that was an unlikely scenario, considering his performance so far. “Or do you need to return home?”

“I...I can keep going.” Aero nodded with a smile, sweat lining his brow and his cock squeezing out another few drops which fell against the patch of multi-colored hair at Cadance’s pussy. The dean flinched and trembled from excitement, her sensitive frame still slowly coming down from a very high peak - the highest she had ever hit. Aero closed his eyes for a moment as he leaned back against his principal, taking in a deep breath as he prepared himself for another round. “But, uh...it’s a long walk back home, and I already missed the bus. And if I wear myself out having sex with both of you…”

“...I suppose we can give you a ride home.” Principal Cinch observed, and continued cradling the boy against her. His cock was certainly hard enough that she could take a ride right then and there, but she was more than content to fondle him, to care for him, and to watch Cadance below them twitching and gasping in her post-orgasmic state. “Perhaps we can even...stop in. And say hello to...those women.”

“To Celestia and Luna?” Aero smiled sweetly, his eyes half-opening as he gazed up at the refined features of Principal Cinch. He leaned forward to press a kiss to the underside of her chin, a tiny reward for her tiny gesture of civility. “I’d like that, Principal Cinch. I want...I want everyone to be friends. I know it’s hard sometimes, but...it’d make me really happy.”

Principal Cinch, despite her most fierce indignations, couldn’t resist such a request. Her fingers tightened around his cock and she squeezed him free of another few drops, cum that she’d be licking off of Cadance’s lap in a few minutes while Aero fucked her from behind. But beyond the excitement running through her, she had to admit...it was nice to see the boy so happy that she was willing to get along with her former enemies.

“Well...your happiness is indeed important.” Principal Cinch murmured, and kissed his brow once more. “So...I will try.”

Thankfully, it seemed like the only thing she’d be fighting with Celestia over anymore was who got to fuck their boy lover first on any given night.

End of Chapter 4.

**Author's Note:**

> Hope you enjoyed! [Please check me out on tumblr.](http://dracedomino.tumblr.com)


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